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A kind of synthetic method of 3-boc-aminomethyl cyclobutanone

A technology of aminomethylcyclobutanone and 3-boc-, which is applied in the field of synthesis of 3-Boc-aminomethylcyclobutanone, can solve the problems of troublesome post-processing and high cost of raw materials

Active Publication Date: 2020-10-20
GL BIOCHEM SHANGHAI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a synthetic method of 3-Boc-aminomethylcyclobutanone, which mainly solves the technical problems of high raw material cost and cumbersome post-processing of existing synthetic methods

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  • A kind of synthetic method of 3-boc-aminomethyl cyclobutanone

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Embodiment 1

[0011] step 1:

[0012] Add 3-oxocyclobutane carboxylic acid (45.0 g, 395 mmol) and methanol (250 mL) to a 500 ml three-necked flask; add trimethyl orthoformate (75 ml, 713 mmol) at room temperature; p-toluenesulfonic acid Monohydrate (2.0 g, 10.5 mmol). After heating under reflux and stirring for 5 hours, the reaction solution was cooled to room temperature, and most of the methanol was spun off, then saturated sodium bicarbonate solution (500 mL) was added, and ethyl acetate (300 mL*2) was added for extraction. The organic phase was separated and the organic phase was separated. (300 mL) and saturated brine (300 ml), and then dried with anhydrous sodium sulfate. The filtrate was spin-dried to obtain a colorless oily liquid, target compound 1 (71.5 g, 411 mmol, 104%). 1 H NMR (400 MHz, CDCl 3 ): 3.71 (s, 3H), 3.17 (d, J=8.2 Hz, 6H), 2.90 (p, J=8.7 Hz, 1H), 2.49-2. 36 (m, 4H).

[0013] Step 2:

[0014] Add compound 1 (60.0 g, 344 mmol) and methanol (500 mL) to a 1000 ml three-neck...

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Abstract

The invention relates to a method for synthesizing 3-(Boc-aminomethyl)cyclobutanone. The method for synthesizing 3-(Boc-aminomethyl)cyclobutanone provided by the invention mainly solves the technicalproblems of high raw material cost and relatively difficult post-processing according to the existing synthesis method. The method for synthesizing 3-(Boc-aminomethyl)cyclobutanone provided by the invention comprises the following steps: 3-oxocyclobutanecarboxylic acid and trimethyl orthoformate are reacted in the methanol solution to generate a compound 1; the compound 1 and benzylamine are reacted in the methanol solution under an action of sodium methoxide to generate a compound 2; the compound 2 and sodium bis(2-methoxyethoxy)aluminiumhydride are reacted in tetrahydrofuran solution to generate a compound 3; the compound 3 is subjected to a Pd / C debenzylation and hydrogenation operation in the methanol solution to obtain a compound 4; the compound 4 and Boc2O are reacted in the methanolsolution to obtain a compound 5; the compound 5 is reacted in a 0.05 M hydrochloric acid solution generate a target compound 6. By performing an enzymatic catalyzed deglandulation action of on the corresponding prochiral 3-substituted cyclobutanone, a series of gamma-butyrolactone derivatives, including some spiro derivatives, can be obtained; and all the derivatives are inhibitors having good biological activity.

Description

Technical field [0001] The present invention relates to the synthesis of 3-Boc-aminomethylcyclobutanone (CAS: 130369-09-4). Background technique [0002] Four-membered ring compounds Highly reactive four-membered ring products include cyclobutane, oxetane, azetidine, etc. These compounds can be functionalized at various positions on the ring, and can be used to design and synthesize a series of biologically active compounds, and have a wide range of applications. For example, L-azetidine-2-carboxylic acid (2133-34-8) is an anti-angiogenesis inhibitor that inhibits collagen synthesis. A series of γ-butyrolactone derivatives can be obtained by enzymatically catalyzing the corresponding prochiral 3-substituted cyclobutanone, including some spiro derivatives, which have good biological activity Inhibitors. [0003] Traditional method [0004] . Summary of the invention [0005] The purpose of the present invention is to provide a method for synthesizing 3-Boc-aminomethylcyclobutanon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C269/06C07C271/18
CPCC07C67/08C07C213/02C07C231/02C07C269/04C07C269/06C07C2601/04C07C271/18C07C271/16C07C217/52C07C235/40C07C69/757
Inventor 徐红岩崇东升王杰郑莉莉
Owner GL BIOCHEM SHANGHAI
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